#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223506.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223506
loop_
_publ_author_name
'Peppel, Tim'
'Köckerling, Martin'
_publ_section_title
;
 3-(1H-Imidazol-1-yl)propanenitrile
;
_journal_coeditor_code           OM2269
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2480
_journal_paper_doi               10.1107/S1600536809035685
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H7 N3'
_chemical_formula_moiety         'C6 H7 N3'
_chemical_formula_sum            'C6 H7 N3'
_chemical_formula_weight         121.15
_chemical_melting_point          310
_chemical_name_systematic
;
3-(1H-Imidazol-1-yl)propanenitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.9790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2712(3)
_cell_length_b                   5.5917(2)
_cell_length_c                   15.4625(5)
_cell_measurement_reflns_used    8906
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.68
_cell_volume                     617.17(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'ct.exe (Köckerling, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker--Nonius X8 Apex'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0092
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11604
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_correction_T_min  0.9464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.157
_refine_ls_extinction_coef       0.064(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.1206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                1456
_reflns_number_total             1542
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2269.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223506
_cod_database_fobs_code          2223506
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.76561(9) 0.25180(10) 0.30688(4) 0.0207(2) Uani d . 1 . .
C C1 0.65410(10) 0.1964(2) 0.22892(5) 0.0254(2) Uani d . 1 . .
H H1 0.579(2) 0.053(2) 0.2217(7) 0.033(3) Uiso d . 1 . .
N N2 0.66230(10) 0.35800(10) 0.16800(4) 0.0302(2) Uani d . 1 . .
C C2 0.78660(10) 0.5266(2) 0.20919(6) 0.0281(2) Uani d . 1 . .
H H2 0.817(2) 0.670(2) 0.1771(8) 0.037(3) Uiso d . 1 . .
C C3 0.85190(10) 0.46480(10) 0.29465(5) 0.0249(2) Uani d . 1 . .
H H3 0.944(2) 0.535(2) 0.3408(8) 0.035(3) Uiso d . 1 . .
C C4 0.78760(10) 0.11150(10) 0.38757(5) 0.0239(2) Uani d . 1 . .
H H4A 0.919(2) 0.109(2) 0.4147(7) 0.030(3) Uiso d . 1 . .
H H4B 0.744(2) -0.051(2) 0.3700(7) 0.031(3) Uiso d . 1 . .
C C5 0.67080(10) 0.2069(2) 0.45232(5) 0.0254(2) Uani d . 1 . .
H H5A 0.683(2) 0.100(2) 0.5022(8) 0.037(3) Uiso d . 1 . .
H H5B 0.538(2) 0.217(2) 0.4243(7) 0.035(3) Uiso d . 1 . .
C C6 0.72980(10) 0.4436(2) 0.48692(5) 0.0244(2) Uani d . 1 . .
N N3 0.77790(10) 0.62750(10) 0.51425(5) 0.0333(2) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0242(3) 0.0212(3) 0.0176(3) 0.0012(2) 0.0061(2) 0.0007(2)
C1 0.0293(4) 0.0279(4) 0.0194(4) 0.0001(3) 0.0057(3) -0.0026(3)
N2 0.0345(4) 0.0371(4) 0.0196(3) 0.0033(3) 0.0064(3) 0.0029(3)
C2 0.0290(4) 0.0307(4) 0.0271(4) 0.0027(3) 0.0113(3) 0.0075(3)
C3 0.0246(4) 0.0249(4) 0.0257(4) -0.0015(3) 0.0065(3) 0.0023(3)
C4 0.0318(4) 0.0213(4) 0.0188(3) 0.0026(3) 0.0058(3) 0.0025(3)
C5 0.0321(4) 0.0265(4) 0.0190(4) -0.0056(3) 0.0084(3) -0.0011(3)
C6 0.0265(4) 0.0288(4) 0.0186(3) 0.0011(3) 0.0060(3) -0.0002(3)
N3 0.0386(4) 0.0303(4) 0.0313(4) -0.0002(3) 0.0078(3) -0.0047(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C3 . . 106.68(6) ?
C1 N1 C4 . . 126.06(7) ?
C3 N1 C4 . . 127.27(7) ?
N2 C1 N1 . . 112.30(7) ?
C1 N2 C2 . . 104.76(7) ?
C3 C2 N2 . . 110.64(7) ?
C2 C3 N1 . . 105.63(7) ?
N1 C4 C5 . . 112.92(6) ?
C6 C5 C4 . . 113.28(7) ?
N3 C6 C5 . . 179.24(9) ?
H1 C1 N2 . . 126.2(7) ?
H1 C1 N1 . . 121.5(7) ?
H2 C2 C3 . . 128.4(7) ?
H2 C2 N2 . . 120.9(7) ?
H3 C3 C2 . . 132.8(7) ?
H3 C3 N1 . . 121.4(7) ?
H4A C4 H4B . . 110.4(9) ?
H4A C4 N1 . . 108.5(7) ?
H4B C4 N1 . . 106.5(7) ?
H4A C4 C5 . . 110.2(7) ?
H4B C4 C5 . . 108.2(7) ?
H5A C5 H5B . . 109.0(10) ?
H5A C5 C6 . . 107.0(7) ?
H5B C5 C6 . . 107.9(7) ?
H5A C5 C4 . . 109.2(7) ?
H5B C5 C4 . . 110.7(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.3540(10) ?
N1 C3 . 1.3760(10) ?
N1 C4 . 1.4565(9) ?
C1 N2 . 1.3150(10) ?
N2 C2 . 1.3760(10) ?
C2 C3 . 1.3610(10) ?
C4 C5 . 1.5270(10) ?
C5 C6 . 1.4610(10) ?
C6 N3 . 1.1410(10) ?
C1 H1 . 0.970(10) ?
C2 H2 . 0.990(10) ?
C3 H3 . 0.970(10) ?
C4 H4A . 0.970(10) ?
C4 H4B . 0.990(10) ?
C5 H5A . 0.970(10) ?
C5 H5B . 0.980(10) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5A N2 4_566 0.970(10) 2.660(10) 3.3660(10) 135.7(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 484448
